I first heard of Michael Saylor in the late 1990s, through CNBC and publications like Investor’s Business Daily. Back then, he was getting a lot of press for founding MicroStrategy, one of the fastest-growing tech companies of the era. When the dot-com bubble burst in the early 2000s, MicroStrategy’s rise slowed. For years, I didn’t hear much about the company—at least not until 2024, when I started learning about Bitcoin.
Reading about his push into Bitcoin made me a believer, and set me on a path to become a serious Bitcoiner myself.
On January 10, 2024, I was watching CNBC and learned that the Securities and Exchange Commission had approved certain financial institutions to begin selling Bitcoin ETFs. I wanted to gain more exposure to BTC immediately upon hearing the news. Unfortunately, I couldn’t move money into my Coinbase account fast enough. Since I couldn’t get cash onto an exchange to buy Bitcoin, I used my E*TRADE account to purchase shares in MicroStrategy. From what I had read, I considered MicroStrategy a kind of derivative play on Bitcoin, and I admired Michael Saylor as an ambassador of the message.
Based on what I’d read about MicroStrategy’s plan, I used leverage to purchase 300 shares of MicroStrategy at $568 per share, for a total investment of $170,400.
Those shares later split 10-for-1, which converted the original 300 shares I purchased into 3,000 shares. By January 16, 2025, they had climbed to $362 per share—worth more than $1,086,000. Unfortunately, I sold those early shares that I purchased too soon. Although I booked a profit, the profit would have been much higher if I had held onto the original purchase.
As CZ has famously said, you can’t get rich if you can’t hold.
Thanks to Michael Saylor’s influence, I continued buying and trading MicroStrategy throughout 2024. As of this writing, I hold 1,000 shares. But I’ve also booked 100s of thousands in profits from trading MicroStrategy and related stocks, and I used those profits to grow my Bitcoin portfolio.
I’ve also learned a great deal from Michael Saylor’s journey into Bitcoin.
When MicroStrategy pivoted to put massive portions of its balance sheet into Bitcoin, Saylor emerged as one of the most vocal advocates for the digital asset. He often describes Bitcoin as “digital property” and “the best asset class” for preserving and multiplying wealth over time. He argues that, unlike fiat currencies continually eroded by inflation, Bitcoin offers a provably scarce digital commodity that serves as a global store of value. He believes its network effects will lead to exponential growth. That’s why he boldly predicts Bitcoin may reach $13 million per coin in the years ahead.
Saylor’s vision resonated with me not simply because of the potential upside, but because of his conviction in building a future based on disruptive innovation. People questioned his early moves—especially when he started converting large swaths of cash into Bitcoin—but over time, his dedication to learning and adaptation proved instrumental to MicroStrategy’s resurgence. That kind of leadership reminds me of how crucial it is to build relationships with people who challenge conventional thinking. We never know where a person’s insights might lead if we’re willing to listen and learn.
Self-Directed Learning Question:
- How are you investing your time and resources right now to build relationships with mentors or advisors whose insights could transform your future?
